The F Word, a new romantic comedy opening Friday, covers familiar romcom territory – about men and women and friendship (or more). But it does so with a rich contemporary quirkiness, and a Canadian perspective. The film was shot in Toronto – proudly playing itself; directed by Canadian Michael Dowse (Goon); and written by Elan Mastai, who was born and raised in Vancouver. He adapted it from the Fringe Festival play Toothpaste and Cigars, by Canadians TJ Dawe and Mike Rinaldi, which Mr. Mastai saw in Vancouver in late 2004.

It also features a superstar actor in the lead role: Daniel Radcliffe plays the heartbroken med-school dropout Wallace to Zoe Kazan’s unavailable (but happy to be friends!) Chantry, an animator.

“I think Elan Mastai … is a very funny, very clever man,” Mr. Radcliffe told me during an interview at the Whistler Film Festival in 2012. “He writes women very well as well. Which is I think obviously very important for a romantic comedy.”

Mr. Mastai, 39, is now based in Toronto (where he’s now writing a screenplay based on an episode of the radio show This American Life). We reached him in B.C., on vacation with his family.

Where were you in your screenwriting career when you saw that play?

When I was growing up in Vancouver, it felt like more of a place that people from Hollywood came to shoot their movies, but it wasn’t really a place where people wrote movies. The idea of being a screenwriter seemed very far away. I didn’t know anybody in the business, I didn’t have any connections, I was really starting from scratch. So when I was starting out I was very much open to whatever job came my way. I was still in university when I got hired to write my first movie. It was a kids’ movie for Keystone, who had done the Air Bud movies; it was called MVP: Most Vertical Primate. That was in late 2000. And in 2005 I’d been working relatively steadily, but it was mostly on work-for-hire jobs. I didn’t feel a huge amount of personal ownership over the material; I was more of a hired gun. So The F Word was the first project where I was going to pursue my own voice instead of writing the version that someone was asking me to write.

How did you become screenwriter-for-hire?

This friend of mine from university was working for this producer. She said, I can’t get you a job but I can get you a meeting. He often looks to meet with young writers and I can at least get you a phone call with him. The phone call went well and the followup meeting went well and I ended up getting hired to write a draft on this kids’ movie. I wrote three drafts in five weeks and every step of the way I assumed I was going to get fired because I didn’t know what I was doing. But there was enough raw energy in those pages that I ended up sticking with it and that movie ended up getting made. The funny thing is, I don’t think this woman totally explained to this producer that I had never written a movie before. I think he just thought I was a screenwriter who had done some stuff and he wouldn’t be on the phone with me if I didn’t know what I was doing. My approach was fake it ’til you make it. In fact, I knew so little that I didn’t really even know how to format a screenplay. I went to a bookstore and I bought the published screenplay for Pulp Fiction. I modelled my first screenplay off of what Quentin [Tarantino] had done. To the point where Pulp Fiction was 134 pages so I made my screenplay 134 pages – which is way too long for a kids’ movie about a skateboarding chimpanzee. In fact, the producer described it as War and Peace with chimps.

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